Pyridine → HCID 22340289, compound

HRID 585318Notes

Reaction equation

HRID 585318 reaction equation
[N:1]1([CH2:6][C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([NH2:17])[CH:13]=3)[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.Cl[C:25](OC1C=CC([N+]([O-])=O)=CC=1)=[O:26].Cl.[F:38][C:39]1[CH:44]=[CH:43][C:42]([CH:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)=[CH:41][CH:40]=1.[OH-].[Na+]>O1CCCC1.O.C(OCC)(=O)C>[F:38][C:39]1[CH:44]=[CH:43][C:42]([CH:45]2[CH2:46][CH2:47][N:48]([C:25]([NH:17][C:12]3[CH:13]=[C:14]4[C:9](=[CH:10][CH:11]=3)[N:8]=[C:7]([CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:16]=[CH:15]4)=[O:26])[CH2:49][CH2:50]2)=[CH:41][CH:40]=1

Participants

9

Reactant 5

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 821294-Nitrophenyl chloroformateHCID 119945322-(1-Pyrrolidinylmethyl)-6-quinolinylamineHCID 218981684-(4-Fluoro-phenyl)-piperidine hydrochloride

Product 1

HCID 22340289HCID 22340289, compoundYield 64.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the 2-(1-pyrrolidinylmethyl)-6-quinolinylamine (500 mg, 2.2 mmol) obtained in Reference Example 9 and pyridine (0.356 ml, 4.4 mmol) in tetrahydrofuran (11 ml) was added 4-nitrophenyl chloroformate (488 mg, 2.42 mmol) under ice-cooling. After stirred for 30 minutes, the reaction solution was concentrated, and dimethyl sulfoxide (11 ml) was added to the residue. 4-(4-Fluorophenyl)piperidine hydrochloride (569 mg, 2.64 mmol) and a 4N aqueous sodium hydroxide solution (0.66 ml) were added thereto at room temperature while stirring, and the mixture was stirred for 2 hours. Ethyl acetate and water were added, the mixture was extracted, the organic layer was washed with water, and concentrated, and the residue was purified by alumina column chromatography (developing solvent: ethyl acetate) to obtain the titled compound (612 mg) as a colorless powder from ethyl acetate-diisopropyl ether.

Workup

  1. temperaturecooling
  2. concentrationthe reaction solution was concentrated
  3. additiondimethyl sulfoxide (11 ml) was added to the residue
  4. stirringat room temperature while stirring
  5. stirringthe mixture was stirred for 2 hours
  6. extractionthe mixture was extracted
  7. washthe organic layer was washed with water
  8. concentrationconcentrated
  9. customthe residue was purified by alumina column chromatography (developing solvent: ethyl acetate)

Sources & evidence

ORD record
ord-fd22fa45b95b4e3896743414d5342e53
Source dataset
uspto-grants-2005_08
Patent number
US06930185B2

Reaction notes

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